JPS6157307B2 - - Google Patents

Info

Publication number: JPS6157307B2
Authority: JP; Japan
Prior art keywords: guanidino; thiazole; imidazolyl; mmol; mixture
Prior art date: 1980-10-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP56163370A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5795972A (en

Inventor

Roorensu Ramatsuchina Jon

Andoryuu Ripinsukii Kurisutofuaa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Inc

Original Assignee

Pfizer Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-10-14

Filing date

1981-10-13

Publication date

1986-12-06

1981-10-13 Application filed by Pfizer Inc filed Critical Pfizer Inc

1982-06-15 Publication of JPS5795972A publication Critical patent/JPS5795972A/ja

1986-12-06 Publication of JPS6157307B2 publication Critical patent/JPS6157307B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 93
239000002253 acid Substances 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
GQOVTZHEZPKTGS-UHFFFAOYSA-N 2-[4-(2-amino-1,3-thiazol-4-yl)-1,3-thiazol-2-yl]guanidine Chemical class S1C(NC(=N)N)=NC(C=2N=C(N)SC=2)=C1 GQOVTZHEZPKTGS-UHFFFAOYSA-N 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
AXCNMJYJGZCULB-UHFFFAOYSA-N 2-[4-(1,3-thiazol-4-yl)-1,3-thiazol-2-yl]guanidine Chemical compound S1C(NC(=N)N)=NC(C=2N=CSC=2)=C1 AXCNMJYJGZCULB-UHFFFAOYSA-N 0.000 claims description 2
LQXWVSXNRXFDKX-UHFFFAOYSA-N 2-[4-[2-(hydroxymethyl)-1h-imidazol-5-yl]-1,3-thiazol-2-yl]guanidine Chemical compound S1C(NC(=N)N)=NC(C=2N=C(CO)NC=2)=C1 LQXWVSXNRXFDKX-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Chemical group 0.000 claims description 2
VQWJQJWRWJGSHN-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1,3-thiazole Chemical compound C1=CNC(C=2SC=CN=2)=N1 VQWJQJWRWJGSHN-UHFFFAOYSA-N 0.000 claims 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
OEVXDSVBHOYPRJ-UHFFFAOYSA-N 2-[4-(2,4-dimethylimidazol-4-yl)-1,3-thiazol-2-yl]guanidine Chemical compound C1=NC(C)=NC1(C)C1=CSC(N=C(N)N)=N1 OEVXDSVBHOYPRJ-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000007787 solid Substances 0.000 description 73
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
239000000203 mixture Substances 0.000 description 59
239000000243 solution Substances 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
238000002844 melting Methods 0.000 description 44
230000008018 melting Effects 0.000 description 44
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
-1 ethanone compound Chemical class 0.000 description 41
238000001914 filtration Methods 0.000 description 40
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
238000010992 reflux Methods 0.000 description 27
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 26
239000002244 precipitate Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 22
239000000543 intermediate Substances 0.000 description 20
239000000706 filtrate Substances 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
238000000354 decomposition reaction Methods 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
229910000029 sodium carbonate Inorganic materials 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
239000002198 insoluble material Substances 0.000 description 13
239000012458 free base Substances 0.000 description 12
239000000463 material Substances 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 11
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 9
239000002585 base Substances 0.000 description 9
OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 9
229910000042 hydrogen bromide Inorganic materials 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
239000002002 slurry Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RGHIROSMHZJRQK-UHFFFAOYSA-N 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylic acid Chemical compound NC(=N)NC1=NC(C(O)=O)=CS1 RGHIROSMHZJRQK-UHFFFAOYSA-N 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
238000011282 treatment Methods 0.000 description 8
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
235000011114 ammonium hydroxide Nutrition 0.000 description 7
238000009835 boiling Methods 0.000 description 7
150000002367 halogens Chemical class 0.000 description 7
150000002431 hydrogen Chemical group 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000003485 histamine H2 receptor antagonist Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
208000008469 Peptic Ulcer Diseases 0.000 description 5
125000005233 alkylalcohol group Chemical group 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
235000008504 concentrate Nutrition 0.000 description 5
239000003480 eluent Substances 0.000 description 5
229960001340 histamine Drugs 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
MZJZNADJWQEIIG-UHFFFAOYSA-N 1-(2-methyl-1h-imidazol-5-yl)ethanone Chemical compound CC(=O)C1=CN=C(C)N1 MZJZNADJWQEIIG-UHFFFAOYSA-N 0.000 description 4
UJLNITKVGULKNI-UHFFFAOYSA-N 2-[4-(hydrazinecarbonyl)-1,3-thiazol-2-yl]guanidine Chemical compound NNC(=O)C1=CSC(NC(N)=N)=N1 UJLNITKVGULKNI-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
206010020601 Hyperchlorhydria Diseases 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
108010079943 Pentagastrin Proteins 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000029142 excretion Effects 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
210000002837 heart atrium Anatomy 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 4
229960000444 pentagastrin Drugs 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
TUFOJIVMBHBZRQ-UHFFFAOYSA-N 1-(1h-imidazol-5-yl)ethanone Chemical compound CC(=O)C1=CN=CN1 TUFOJIVMBHBZRQ-UHFFFAOYSA-N 0.000 description 3
SGXWMBXNTCVZPY-UHFFFAOYSA-N 1-(2,4-dimethylimidazol-1-yl)ethanone Chemical compound CC(=O)N1C=C(C)N=C1C SGXWMBXNTCVZPY-UHFFFAOYSA-N 0.000 description 3
HEUBFSYOZRPRTD-UHFFFAOYSA-N 1-(2,5-dimethyl-1h-imidazol-4-yl)ethanone Chemical compound CC(=O)C=1NC(C)=NC=1C HEUBFSYOZRPRTD-UHFFFAOYSA-N 0.000 description 3
HUKNDBAKSCHISX-UHFFFAOYSA-N 1-(5-methyl-1h-imidazol-4-yl)ethanone Chemical compound CC(=O)C=1N=CNC=1C HUKNDBAKSCHISX-UHFFFAOYSA-N 0.000 description 3
MGSUZKWFACFSDH-UHFFFAOYSA-N 1-[2-(hydroxymethyl)-1h-imidazol-5-yl]ethanone Chemical compound CC(=O)C1=CNC(CO)=N1 MGSUZKWFACFSDH-UHFFFAOYSA-N 0.000 description 3
QTVGLOOZIYZYRQ-UHFFFAOYSA-N 2-bromo-1-[2-(hydroxymethyl)-1h-imidazol-5-yl]ethanone;hydrobromide Chemical compound Br.OCC1=NC(C(=O)CBr)=CN1 QTVGLOOZIYZYRQ-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
LBSBQVAGEVSBQP-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(N=C(N)N)=N1 LBSBQVAGEVSBQP-UHFFFAOYSA-N 0.000 description 3
VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
229910000039 hydrogen halide Inorganic materials 0.000 description 3
239000012433 hydrogen halide Substances 0.000 description 3
238000001802 infusion Methods 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
RYYCFQTWLMFJIG-UHFFFAOYSA-N propylcyanamide Chemical compound CCCNC#N RYYCFQTWLMFJIG-UHFFFAOYSA-N 0.000 description 3
239000010453 quartz Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000002731 stomach secretion inhibitor Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000001665 trituration Methods 0.000 description 3
229910052727 yttrium Inorganic materials 0.000 description 3
RROBYWWPVULLSU-UHFFFAOYSA-N 2-[4-(1h-imidazol-5-yl)-1,3-thiazol-2-yl]guanidine Chemical compound S1C(NC(=N)N)=NC(C=2N=CNC=2)=C1 RROBYWWPVULLSU-UHFFFAOYSA-N 0.000 description 2
FQOXJJNWHXRGIV-UHFFFAOYSA-N 2-[4-(2-aminoacetyl)-1,3-thiazol-2-yl]guanidine;dihydrochloride Chemical compound Cl.Cl.NCC(=O)C1=CSC(NC(N)=N)=N1 FQOXJJNWHXRGIV-UHFFFAOYSA-N 0.000 description 2
HNCBHFLGVNAVNT-UHFFFAOYSA-N 2-[4-(2-bromoacetyl)-1,3-thiazol-2-yl]guanidine;hydrobromide Chemical compound Br.NC(=N)NC1=NC(C(=O)CBr)=CS1 HNCBHFLGVNAVNT-UHFFFAOYSA-N 0.000 description 2
YQWRPDMPXIRUSH-UHFFFAOYSA-N 2-[4-(5-methyl-1h-imidazol-4-yl)-1,3-thiazol-2-yl]guanidine;hydrobromide Chemical compound Br.N1=CNC(C=2N=C(NC(N)=N)SC=2)=C1C YQWRPDMPXIRUSH-UHFFFAOYSA-N 0.000 description 2
YIUSMHXFPSORGW-UHFFFAOYSA-N 2-[4-(5-propyl-1h-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]guanidine Chemical compound CCCC1=NNC(C=2N=C(NC(N)=N)SC=2)=N1 YIUSMHXFPSORGW-UHFFFAOYSA-N 0.000 description 2
UDFQWTOIRFJRHP-UHFFFAOYSA-N 2-[4-[2-(hydroxymethyl)-1h-imidazol-5-yl]-1,3-thiazol-2-yl]guanidine;hydrobromide Chemical compound Br.S1C(NC(=N)N)=NC(C=2N=C(CO)NC=2)=C1 UDFQWTOIRFJRHP-UHFFFAOYSA-N 0.000 description 2
MVTGVDHNHMILAT-UHFFFAOYSA-N 2-bromo-1-(2-methyl-1h-imidazol-5-yl)ethanone;hydrobromide Chemical compound Br.CC1=NC(C(=O)CBr)=CN1 MVTGVDHNHMILAT-UHFFFAOYSA-N 0.000 description 2
NHZTZQDWMOWTJF-UHFFFAOYSA-N 2-bromo-1-(5-methyl-1h-imidazol-4-yl)ethanone Chemical compound CC=1N=CNC=1C(=O)CBr NHZTZQDWMOWTJF-UHFFFAOYSA-N 0.000 description 2
DRWDZFNIPARKSG-UHFFFAOYSA-N 2-hydroxyethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CO DRWDZFNIPARKSG-UHFFFAOYSA-N 0.000 description 2
ILURHDNYPWZLFB-UHFFFAOYSA-N 2-phenylethylcyanamide Chemical compound N#CNCCC1=CC=CC=C1 ILURHDNYPWZLFB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
QIRSDXBXWUTMRE-UHFFFAOYSA-N benzylcyanamide Chemical compound N#CNCC1=CC=CC=C1 QIRSDXBXWUTMRE-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
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239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP56163370A 1980-10-14 1981-10-13 2-guanidino-4-heteroarylthiazole compound Granted JPS5795972A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US19623180A	1980-10-14	1980-10-14

Publications (2)

Publication Number	Publication Date
JPS5795972A JPS5795972A (en)	1982-06-15
JPS6157307B2 true JPS6157307B2 (ko)	1986-12-06

Family

ID=22724544

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56163370A Granted JPS5795972A (en)	1980-10-14	1981-10-13	2-guanidino-4-heteroarylthiazole compound

Country Status (6)

Country	Link
JP (1)	JPS5795972A (ko)
HU (2)	HU191496B (ko)
IN (2)	IN163170B (ko)
PL (1)	PL135097B1 (ko)
SU (3)	SU1205768A3 (ko)
ZA (1)	ZA817047B (ko)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988003140A1 (en) *	1986-10-29	1988-05-05	Pfizer Inc.	Crystalline 2-(1-pentyl-3-guanidino)-4-(2-methyl-4-imidazolyl)thiazole dihydrochloride trihydrate
IL95548A0 (en) *	1989-09-15	1991-06-30	Fujisawa Pharmaceutical Co	Thiazole derivatives,processes for the preparation thereof and pharmaceutical composition containing the same
US9499533B2 (en)	2012-03-27	2016-11-22	Shionogi & Co., Ltd.	Aromatic 5-membered heterocyclic derivative having TRPV4-Inhibiting activity

1981
- 1981-09-07 IN IN572/DEL/81A patent/IN163170B/en unknown
- 1981-10-13 HU HU833917A patent/HU191496B/hu not_active IP Right Cessation
- 1981-10-13 ZA ZA817047A patent/ZA817047B/xx unknown
- 1981-10-13 JP JP56163370A patent/JPS5795972A/ja active Granted
- 1981-10-13 HU HU833916A patent/HU192826B/hu not_active IP Right Cessation
- 1981-10-14 PL PL24164581A patent/PL135097B1/pl unknown
1982
- 1982-09-17 SU SU823495554A patent/SU1205768A3/ru active
- 1982-09-17 SU SU823491025A patent/SU1311621A3/ru active
- 1982-09-17 SU SU823493197A patent/SU1217258A3/ru active
1985
- 1985-02-13 IN IN120/DEL/85A patent/IN163394B/en unknown

Also Published As

Publication number	Publication date
IN163170B (ko)	1988-08-20
HU191496B (en)	1987-02-27
SU1311621A3 (ru)	1987-05-15
PL135097B1 (en)	1985-09-30
SU1205768A3 (ru)	1986-01-15
ZA817047B (en)	1982-09-29
SU1217258A3 (ru)	1986-03-07
HU192826B (en)	1987-07-28
IN163394B (ko)	1988-09-17
JPS5795972A (en)	1982-06-15
PL241645A1 (en)	1983-11-21

Publication	Publication Date	Title
EP0050458B1 (en)	1985-01-02	2-guanidino-4-heteroarylthiazoles and pharmaceutical compositions containing them
EP0161841B1 (en)	1989-07-19	2-(n-substituteguanidino)-4-hetero-arylthiazole antiulcer agents
HU184259B (en)	1984-07-30	Process for producing 2-imidazoline derivatives
HU212302B (en)	1996-05-28	Process for producing imidazole guanidine derivatives and pharmaceutical compositions containing them
EP0094191B1 (en)	1988-04-20	Antiulcer 2-guanidino-4-(2-substituted-amino-4-imidazolyl)-thiazoles and process therefor
GB2096987A (en)	1982-10-27	Substituted imidazole and imidazole derivatives and their preparation and use
US5025015A (en)	1991-06-18	Thioformamidines, and use as medicaments
JPS60105672A (ja)	1985-06-11	胃抗分泌剤としてのチアトリアジンジオキサイド類
EP0102227B1 (en)	1989-05-03	2(1h)-pyridinones, useful as cardiotonic agents, and their production
JPS6157307B2 (ko)	1986-12-06
US4590299A (en)	1986-05-20	2-guanidino-4-heteroarylthiazoles
DE3336409A1 (de)	1985-04-18	Chinazolinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
HU201059B (en)	1990-09-28	Process for producing 6-oxo-pyridazine derivatives and pharmaceutical compositions containing them
EP0074229B1 (en)	1986-04-09	Triazole gastric anti-secretory agents
US4452987A (en)	1984-06-05	Haloacetyl imidazoles
US4808727A (en)	1989-02-28	Imidazolium hydrogen carbonates
US4510313A (en)	1985-04-09	2-Guanidino-4-heteroarylthiazoles
US4468399A (en)	1984-08-28	2-[2-(2-Aminoalkyl-4-thiazolylmethylthio)alkyl]-amino-5-substituted-4-pyrimidones
NZ207258A (en)	1985-02-28	Substituted imidazoles
JPH0680041B2 (ja)	1994-10-12	２−ピリジル酢酸誘導体、その製法およびそれを含む医薬
NZ207257A (en)	1985-02-28	2-guanidino-thiazoles
JPH02304086A (ja)	1990-12-17	ジアジン誘導体、それらの製造方法およびそれらの化合物を含む医薬
US4544659A (en)	1985-10-01	Schistosomicidal acridanone hydrazones
DE2628642A1 (de)	1977-12-29	In 2-stellung substituierte 1,3-diazacycloverbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CS235969B2 (cs)	1985-05-15	Způsob výroby 2-guanidino-4-thiazolylthiazolů